119 properties available

Located in Ashland, New York, United States. ORCHARD SUITE - Private, Safe & Comfortable Getaway! Hot tub, Pet friendly Applinger Farm is a great gathering place for the any season. RELAX with beautiful views of the Siskiyou & the Cascade snow capped mountains! In the Rogue Valley nestled between the Oregon Shakespeare Festival in Ashland (3.9 mi) & Britt Festival, Jacksonville (13 mi). Easy to find off I-5, this Farm House Suite is comfortable for a great get away! Big outside areas. Enjoy birds and wildlife or beautiful sunrise & sunsets. Relax with Mountain views and horses grazing in the field or turn on your music and laugh loudly to your heart's content.The spaceYou'll have a 8'x10' Deck with table & chairs... the perfect place to have some quiet time, read, work or relax, kitchenette, King Bed, private bathroom, and 32"TV with a king Bedroom Guest access Very large lawn (perfect for games) & large shade trees. Big backyard with a large lawn with views of the Mountains and orchards surrounding our green pastures. Great

Located in Ashland, New York, United States. Garden View Apartment in Gated Castle Community Welcome to the Carriage House Miranda at Chateau Herbe! A state-of-the art contemporary castle estate with stunning grounds This comfortable carriage house apartment is nestled in a gated castle community that boasts classical gardens, orchards, vineyards, water features, and breathtaking mountain views. The property is located minutes from I-5 and downtown Ashland.Please note that this is a shot gun apartment. You must walk through the bedroom with the king bed to get to the bunk bed bedroom.You will have access to the main chateau's sunroom, library, coffee bar, and patio. Explore the vineyard, gardens, orchards, pond pergola, and classical fountain.There are other guests and tenants staying on the property.

Located in Ashland, New York, United States. Craftsman Style Home in Country Setting Nestled between rolling hills and pastures is a special place where you will discover a quality of life matched only by the postcard views from every window. Guests enjoy soothing views of gardens, pastures, and winter snow-capped Mount Ashland. This modern country environment provides an unsurpassed level of comfort, style, and technology; the perfect setting to stay connected with family and friends. Our home shares sixteen acres of flowers, trees and shrub gardens with Valley View Nursery; and is located 4 short miles (10 minutes) from picturesque downtown Ashland, Oregon; home of the Oregon Shakespeare Festival.

Located in Ashland, New York, United States. Mexico Apartment at Wood Hamlet. Lovely gardens. 10 minute walk to town. Warm and colorful unit filled with Mexican folkart. Stunning gardens with private areas and a pond for swimming. Short walk to town for theater, arts, 72-acre Lithia Park, shopping and restaurants.Feel the welcoming warmth of the hand-crafted Mexican decor. Basement unit but with lots of windows and light. (3 beams at 6"1") Kitchen, with top of the line induction burner, fridge, microwave..., full bath, W/Dryer, work area... Wi-fi. Private off-street parking.(Ashland City Permit# 17-080) NO SMOKING ON PREMISESNOTE: guest must be 13 or older in light of unattended pool/pond on propertyThe SpaceThe Mexico Apartment is a basement unit so you must be able to walk down the stairs to enter. It is a comfortable space filled with light at an affordable price from which you can make your forays into town for theater (The Oregon Shakespeare Festival), art, shopping and dining. And use it as a base from which to explore the

Located in Ashland, New York, United States. 3 Bedroom Home - Walking distance to everything - Quiet on dead end street This fully furnished 3 bedroom home has the benefits of a great location: 20 minute walk to downtown, 5 minute walk to the Farmers Market, SOU, science museum and more. And it's in a quiet, picturesque neighborhood on a dead end street. Central air and 2 air filters provide comfort in the summer. You will have full privacy with no one else living on the property. There is a master bedroom with a king bed and private bath, a bedroom with a queen bed and a bedroom with a twin loft bed. The first floor's open design with a large living room that flows into the kitchen makes for a very livable space. The kitchen is spacious with a large island for easy cooking. Kitchen table and table on the deck are immediately next to the kitchen for ease. This is a warm, welcoming home ready for you to move into for a month.

Located in Ashland, New York, United States. Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 2 Within a 5-minute walk, you will discover exceptional restaurants, the Oregon Shakespeare Festival, curio stores, bakeries coffee houses, cafes, bookstores, 4-screen art house movie theater & summer Saturday Farmer's Market. Within a 10 minutes walk enjoy the Food Co-Op, nature shops, pet stores, veterinarians, yoga studios, gyms, the Carnegie-Melon library.Adjacent to Downtown Ashland and Lithia Park. Private room includes separate kitchen with sitting room. Full bath. Two beds. Cable TV with 200 channels +. Self contained and independent ductless mini-split heating and cooling system in the room. Enter sanctuary with outdoor sink with hot water at private entrance. Coffee maker, oven, microwave, electric tea kettle, ice maker. Exceptional lighting. Very quiet. All new construction. Shared washer/dryer. Suite 2 has high ceilings, exceptional lighting, and a super unique ground level view out of one set of windows. The

Located in Ashland, New York, United States. Charming historic cottage just 4 blocks from downtown (Licensed PA 17-248) Whimsical and comfortable cottage located off a quiet alley behind our main residence. You will experience a low-key, friendly neighborhood in the heart of Ashland's Skidmore Historic District. Private garden area with back patio, outside dining for two. You can park your car and never get back in until it's time to leave. Just a 5-10 minute stroll the Ashland Co-op, restaurants, and of course Oregon Shakespeare festival.Full kitchen and laundry. Along with the queen bed there is a single bed in the nook off the living area for a 3rd person or for those who prefer to sleep separately. The closet has lots of shelving to store your things. Bathe in the claw-foot tub or use the shower. Heat and AC keeps things comfortable. This is a light-filled groovy hideaway.Parking is out on the street about 200 feet from the cottage.Monthly rentals are not available except in rare circumstances and only for one pers

Located in Ashland, New York, United States. The Dogwood Suite at Tudor House Vacation Rentals The upstairs Bedroom has a queen and a twin bed. The downstairs has a full kitchen, dining table, sofa-bed, and TV. Free WIFI is available throughout the house, and it has central heat and Air Conditioning.The off-street parking lot behind the house is a great place to leave your car for your visit, the 1/2 mile walk to downtown is nice and level and mostly along Siskiyou Boulevard.

Located in Ashland, New York, United States. Luxurious Living: 4BR Gem, HotTub, Gym Welcome to our luxurious and tranquil retreat, featuring two stunning master bedrooms. One bedroom boasts a jetted tub in its en suite bathroom, while the other features French doors leading out to the pool area.Our home offers 4 brand new king beds and 2 queen-sized fold-out couches, accommodating up to 12 guests in comfort and style. The spacious living room, dining room, and kitchen provide ample space for enjoying time with friends and family.Step outside to our inviting outdoor area, complete with a large table and chairs, a bistro table, a barbecue, a heat lamp, and plenty of comfortable seating. Relax in our hot tub or seasonal pool with loungers, or take advantage of our well-equipped home gym with a lifting rig, dumbbells, kettlebells, boxing gloves and mitts, Peloton bike, and a 2-person sauna in the garage.If you are in need of a car rental, we are pleased to offer our available Hyundai Palisade for separate rental. The car will be conv

Located in Ashland, New York, United States. 1 MONTH MINIMUM UPSTAIRS APARTMENT IN VICTORIAN HOUSE This furnished apartment is spacious and airy. There is a separate entrance to the apartment. There are 2 bedrooms, a full kitchen , an outdoor deck, cable tv, wi-fi, off-street parking. Views of the mountains from the windows and the deck. The apartment is half a block from Garfield Park, 3 blocks from Southern Oregon University, and an easy 20 minute walk to the center of town. Month to month rental

Located in Ashland, New York, United States. Private and quiet luxury studio suite on three acres overlooking Ashland. Located on three acres overlooking Ashland, yet just minutes away from everything Ashland has to offer, this private luxury suite offers the best of all worlds. With a separate access, private patio, dedicated parking, and close to the best hiking and walking trails near Ashland, this quiet retreat will make you never want to leave. Feel pampered and relaxed with marble, heated floors in the bathroom, an oversized tub/shower and commode room with bidet toilet. Whether you're planning a white water rafting excursion, Shakespearean play or an incredible meal at one of Ashland's many excellent restaurants, you'll want to come back and recharge in this special place. And did I mention the views? Just incredible! Need more space? Ask me about my other short term rental on the same property.

Located in Ashland, New York, United States. The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean 3 bedroom, 2 bath villa on acreage within minutes of theaters, restaurants and shopping. Very private with modern kitchen, hd tv w/ Dish network, high speed internet. Caretaker lives in separate structure on site. Ashland's best forest walking trails are only steps away. Magnificent 180 degree views of the valley, city lights, orchards and vineyards. Single level detached dwelling with plenty of paved parking. Minimum 3 night rental.

Located in Ashland, New York, United States. Budget-friendly Stay in Oregon Near Oregon Shakespeare Festival | Free Parking Explore vibrant Ashland from our doorstep, conveniently located off Interstate 5 and Route 99, just twenty minutes from the California-Oregon border. We're also near Ashland Vineyards and Winery and the Oregon Shakespeare Festival, ensuring you'll never lack for entertainment.Step into your cozy, affordable room at our Ashland oasis, where comfort meets value just off Highway 5. With inviting bed, free WiFi, and all the essentials like air conditioning and flat-screen TVs, your stay promises to be as convenient as it is comfortable. You can also enjoy complimentary coffee in lobby.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of USD 200/stay/unit on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Earl

Located in Ashland, New York, United States. Affordable Stay Ideal For Oregon Retreat | Located at I-5 & Route 99 Explore vibrant Ashland from our doorstep, conveniently located off Interstate 5 and Route 99, just twenty minutes from the California-Oregon border. We're also near Ashland Vineyards and Winery and the Oregon Shakespeare Festival, ensuring you'll never lack for entertainment.Step into your cozy, affordable room at our Ashland oasis, where comfort meets value just off Highway 5. With inviting bed, free WiFi, and all the essentials like air conditioning and flat-screen TVs, your stay promises to be as convenient as it is comfortable. You can also enjoy complimentary coffee in lobby.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residential or apartment accommodations.- The property requires a damage deposit of USD 200/stay/unit on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in

Located in Ashland, New York, United States. Sunset Chalet - 2600 sq.ft. Multi-Seasonal retreat only15 minutes from Ashland ! Sunset Chalet is nestled in the Cascade Mountains at 4000' elevation. Fantastic views overlooking Siskiyou Mtns, Klamath Mtns, Colestine Valley and Mt. Ashland. Awesome sunsets! Perfect for hikers (5 minutes from Pacific Crest Trail and Cascade-Siskiyou National Monument/ Pilot Rock), bikers (dozens of trails from Mt. Ashland down to city of Ashland), skiers (Mt. Ashland Lodge is 15 minutes away), rafters (Klamath River put-in is 30 minutes south) and Shakespearean types who prefer privacy with a view! 15 minutes from Ashland down the I-5 Siskiyou Summit.Chalet has 1000 sq. ft. deck and is located in the Cascade Mountains and built so as not to change the natural surroundings.Why the Owner Chose Ashland: This property has been a dream project. I purchased the bare land in 2007 and began construction in the Fall of that year. The Chalet was completed in February 2009. As with all new construction on acreag

Located in Ashland, New York, United States. Luxury family retreat: Siskiyou Mountain Place. 2 br, kitchenette. Lower prices For more details/photographs/discounts, go to siskiyoumountainplace.com.Siskiyou Mountain Place vacation rental, located southeast of Ashland, includes a fully furnished large main room with kitchenette, dining area and 175 square foot covered deck, full custom bathroom, one bedroom with king bed, another with two queens and a sitting area, all with BRAND NEW beds/bedding, furnishing, fixtures and appliances. New AC/heat system, ceiling fans, crank-open double-pane windows for a cool breeze. Enjoy a shaded panoramic view toward Grizzly Peak and Emigrant Lake, plus spectacular sunsets. VISIT siskiyoumountainplace.com FOR MORE INFORMATION. We provide a wide range of other amenities: Complete bedroom and bathroom linens, fully equipped kitchenette including complimentary welcome basket, variety-pak coffees and teas. Wi-Fi and satellite TV. Private guest access. Pillows and beds protected and sanitized

Located in Ashland, New York, United States. Callahan's House Just a quick walk across the street from your private house to the main lodge, all while still being able to enjoy all the features and amenities the lodge has to offer. This Callahan House is perfect for large families or friends to gather or even use as a bridal suite

Located in Ashland, New York, United States. The Red Dragon House The Red Dragon House is a great location for those who wish to discover Ashland, along with the southern Rogue Valley, but still get that rural feeling while remaining only minutes from town. The single-story house is spacious at nearly 1,000 square feet, and features mountain views of the southern Rogue Valley. The house features a large open living room/kichen area, with lots of counter space, two well-appointed bedrooms and a bathroom shower, suitable for those with mild handicaps, and has three decks from which to choose, all on a property that is 5.2 acres, in a rural neighborhood, that's quiet. All this only five minutes from the nearest restaurants and markets, and ten minutes from Downtown Ashland, and the Mt. Ashland Ski Area is only 19 miles away!While the neighborhood is quiet, it should be mentioned that the property is adjacent to I-5, which makes getting to us easy, but does provide some road noise. So, if it's total quiet you require, this may not b

Located in Ashland, New York, United States. ArtYCottage - custom furniture and art through out. Secluded and fabulous! We now require guests to be vaccinated for Covid 19 and be willing to show proof. No exceptions.The nightly rate is $195.00 for 2 people. Additional guests are $50.00 per guest per night. The maximum number of guests is 4 total. There is a $100.00 cleaning fee for short term stays 2 weeks or less. For longer term stays the fee is $250. There is a 4 day minimum stay.PETS ..... we do allow pets but they are not allowed upstairs or on the furniture. They can be left in the cottage with our approval.We are 6.9 miles out of Ashland. Depending on how you drive it is 10 minutes into shopping and another 5 minutes to downtown. CUSTOM COUNTRY COTTAGE .........as seen in Sunset magazine and Southern Oregon MagazinePLEASE FEEL FREE TO CONTACT US FOR LAST MINUTE SPECIALS IF THE DATES ARE AVAILABLE WE MAY DISCOUNT THEM. FOR OFF SEASON OR DEPENDING ON YOUR LENGTH OF STAYLOCATED:Ten minutes drive from Ashland in the cascade f

Located in Ashland, New York, United States. Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed. Built in the early 1900's and fully renovated The Blue Moon House has it all! Five bedrooms, each with it's own private bathroom. A gourmet kitchen with a large dining area, a living area with a fireplace, large 'smart' flat screen television and plenty of seating. Outdoors enjoy the gardens and the large deck area with more seating and private parking.

Located in Ashland, New York, United States. 2 bedroom cabin, huge deck, lodge-style furnishings. With Suites Trinity, you and your guests will enjoy the entire second floor of Plaza North. Consisting of three separate suites each with its own fully appointed modern kitchen, state-of-the-art fireplace, high ceilings, bright spaces, and large picture windows with gorgeous mountain views. Plus covered parking just steps from secured foyer with elevator to the 2nd floor with adjacent fast charging stations.

Located in Ashland, New York, United States. Cheerful farmhouse villa on 11 acres Forget your worries in this spacious and serene space. Villa on 11 acres surrounded by natural Beauty. Lots of oak trees on the property, hike trails and magnificent view of the rogue valley. enjoy your stay!

Located in Ashland, New York, United States. Lodge Room 2 with Jacuzzi Tub at Green Springs Inn Welcome to Lodge Room 2 at Green Springs Inn! Our comfortable and private room is located in the main lodge of the Green Springs Inn, an ideal hub for your mountain adventures. This dog-friendly room features a king bed and a full bath, as well as comfortable seating and a small desk. The room also includes a private deck with an in-room spa, perfect for relaxing after a day of exploring the nearby trails. Each room also has a mini-fridge, microwave, and coffee maker for your convenience.Green Springs Inn is nestled on over 100 acres in the Cascade-Siskiyou National Monument. Our nature-immersive micro-resort is tucked away in one of the most biologically diverse areas in North America. We take land stewardship seriously, and we know you do too. Please respect the land and thank you in advance for following all of our rules. We have these rules to protect the land, ourselves, our guests, and our community.Please be advised that all gue

Located in Ashland, New York, United States. Agate Flats Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn This dog-friendly, custom cabin sleeps up to 6 guests, with a king-sized bed in the primary bedroom and a queen-sized bed in the loft. The loft area is accessed via a ship ladder staircase. A leather sofa pulls out into a full-sized bed, and twin beds are available by request for use on the sun deck as the seasons allow. This cabin features a deep jetted hot tub located on the private deck. You’ll appreciate the breathtaking views, wood-burning stove and fully appointed kitchen. 
A note about our location: We are located 17 miles east of Ashland, about a 25-30 minute drive on Highway 66 which winds up a mountainside. The drive is stunningly beautiful, but we want to make sure guests know that we are not located inside Ashland city limits.